Application of Azodicarboxylates in Organic Synthesis

doi:10.6023/cjoc1110313

Abstract

Azodicarboxylates, as versatile reagents, have been widely used in organic synthesis due to their unique electronic and structural properties. They have played important roles in organic synthesis such as Mitsunobu reaction, amination of carbonyl compounds and unsaturated hydrocarbons, synthesis of heterocyclic compounds. Besides these, azodicarboxylates can be used as oxidants for the dehydrogenation of alcohols and amines. Based on their previous applications, new progress of azodicarboxylates in synthetic chemistry in recent years is summarized and an outlook on their development is also given.

Key words: azodicarboxylates, organic synthesis, C—N bond formation

Cite this article

Xu Xiaoliang, Cheng Guohua, Li Xiaonian. Application of Azodicarboxylates in Organic Synthesis[J]. Chin. J. Org. Chem., 2012, 32(06): 1024-1040.

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[1] (a) Mitsunobu, O.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc.Jpn. 1967, 40, 935.(b) Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40,2380.(c) Mitsunobu, O.; Eguchi, M. Bull. Chem. Soc. Jpn. 1971, 44,3427.(d) Mitsunobu, O. Synthesis 1981, 1.
[2] (a) Dandapani, S.; Curran, D. P. Chem. Eur. J. 2004, 10, 3130.(b) Dembinski, R. Eur. J. Org. Chem. 2004, 2763.(c) But, T. Y. S.; Toy, P. H. Chem. Asian J. 2007, 2, 1340.
[3] (a) Huisgen, R.; Jakob, F. Justus Liebigs Ann. Chem. 1954, 590, 37.(b) Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986,108, 6394.(c) Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. J. Am.Chem. Soc. 1986, 108, 6395.(d) Trimble, L. A.; Vederas, J. C. J. Am. Chem. Soc. 1986, 108,6397.(e) Evans, D. A.; Nelson, S. G.. J. Am. Chem. Soc. 1997, 119, 6452.(f) Evans, D. A.; Johnson, D. S. Org. Lett. 1999, 1, 595.(g) Yamashita, Y.; Ishitani, H.; Kobayashi, S. Can. J. Chem. 2000,78, 666.
[4] (a) List, B. J. Am. Chem. Soc. 2002, 124, 5656.(b) B?gevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; J?rgensen,K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.(c) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; B?gevig, A.;J?rgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254.(d) Liu, T. Y.; Cui, H. L.; Zhang, Y.; Jiang, K.; Du, W.; He, Z. Q.;Chen, Y. C. Org. Lett. 2007, 9, 3671.(e) Hayashi, Y.; Aratake, S.; Imai, Y.; Hibino, K.; Chen, Q. Y.;Yamaguchi, J.; Uchimaru, T. Chem. Asian J. 2008, 3 225.(f) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003,2448.(g) Baumann, T.; Vogt, H.; Brase, S. Eur. J. Org. Chem. 2007, 266.(h) Baumann, T.; Bachle, M.; Hartmann, C.; Brase, S. Eur. J. Org.Chem. 2008, 2207.(i) Hartmann, C. E.; Baumann, T.; Bachle, M.; Brase, S. Tetrahedron:Asymmetry 2010, 21, 1341.(j) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F. Org. Lett.2003, 5, 1685.(k) Chowdari, N. S.; Barbas, C. F. Org. Lett. 2005, 7, 867.(l) Suri, J. T.; Steiner, D. D.; Barbas, C. F. Org. Lett. 2005, 7, 3885.(m) Kotru z, P.; Alemayehu, S.; Toma, S.; Schmalz, H. G.; Adler, A.Eur. J. Org. Chem. 2005, 4904.

[5] (a) Dahlin, N.; B?gevig, A.; Adolfsson, H. Adv. Synth. Catal. 2004,346, 1101.(b) Franzen, J.; Marigo, M.; Fielenbach, D.; Wabnitz, T. C.;Kj?rsgaard, A.; J?rgensen, K. A. J. Am. Chem. Soc. 2005, 127,18296.(c) Ding, X.; Jiang, H. L.; Zhu, C. J.; Cheng, Y. X. TetrahedronLett. 2010, 51, 6105.(d) Liu, P. M.; Chang, C.; Reddy, R. J.; Ting, Y. F.; Kuan, H. H.;Chen, K. Eur. J. Org. Chem. 2010, 42.(e) Thomassigny, C.; Prim, D.; Greck, C. Tetrahedron Lett. 2006,47, 1117.(f) Gosiewska, S.; Soni, R.; Clarkson, G. J.; Wills, M. TetrahedronLett. 2010, 51, 4214.(g) Fu, J. Y.; Huang, Q. C.; Wang, Q. W.; Wang, L. X.; Xu, X. Y.Tetrahedron Lett. 2010, 51, 4870.(h) Fu, J. Y.; Xu, X. Y.; Li, Y. C.; Huang, Q. C.; Wang, L. X. Org.Biomol. Chem. 2010, 8, 4524.(i) Fu, J. Y.; Yang, Q. C.; Wang, Q. L.; Ming, J. N.; Wang, F. Y.; Xu,X. Y.; Wang, L. X. J. Org. Chem. 2011, 76, 4661.(j) Liu, C.; Zhu, Q.; Huang, K. W.; Lu, Y. X. Org. Lett. 2011, 13,2638.(k) Makino, K.; Kubota, S.; Hara, S.; Sakaguchi, M.; Hamajima, A.;Hamada, Y. Tetrahedron 2009, 65, 9468.(l) Iwamura, H.; Mathew, S. P.; Blackmond, D. G. J. Am. Chem.Soc. 2004, 126, 11770.(m) Blackmond, D. G.; Moran, A.; Hughes, M.; Armstrong, A. J.Am. Chem. Soc. 2010, 132, 7598.

[6] (a) Lee, D.; Otte, R. D. J. Org. Chem. 2004, 69, 3569.(b) Kim, Y. J.; Lee, D. Org. Lett. 2004, 6, 4351.(c) Ni, B.; Zhang, Q. Y.; Garre, S.; Headley, A. D. Adv. Synth.Catal. 2009, 351, 875.

[7] (a) Juhl, K.; J?rgensen, K. A. J. Am. Chem. Soc. 2002, 124, 2420.(b) Marigo, M.; Juhl, K.; J?rgensen, K. A. Angew. Chem., Int. Ed.2003, 42, 1367.(c) Bernardi, L.; Zhuang, W.; J?rgensen, K. A. J. Am. Chem. Soc.2005, 127, 5772.(d) Mashiko, T.; Hara, K.; Tanaka, D.; Fujiwara, Y.; Kumagai, N.;Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 11342.(e) Mashiko, T.; Kumagai, N.; Shibasaki, M. Org. Lett. 2008, 10,2725.(f) Mashiko, T.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc.2009, 131, 14990.(g) Comelles, J.; Pericas, A.; Moreno-Manas, M.; Vallribera, A.;Drudis-Sole, G.; Lledos, A.; Parella, T.; Roglans, A.; Garcla-Granda, S.; Roces-Fernandez, L. J. Org. Chem. 2007, 72, 2077.(h) Terada, M.; Nakano, M.; Ube, H. J. Am. Chem. Soc. 2006, 128,16044.(i) He, R. J.; Wang, X. S.; Hashimoto, T.; Maruoka, K. Angew.Chem., Int. Ed. 2008, 47, 9466.(j) Konishi, H.; Lam, T. Y.; Malerich, J. P.; Rawal, V. H. Org. Lett.2010, 12, 2028.(k) Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2006, 47, 4565.(l) Jung, S. H.; Kim, D. Y. Tetrahedron Lett. 2008, 49, 5527.(m) Ghosh, S.; Nandakumar, M. V.; Krautscheid, H.; Schneider, C.Tetrahedron Lett. 2010, 51, 1860.

[8] (a) Saaby, S.; Bella, M.; J?rgensen, K. A. J. Am. Chem. Soc. 2004,126, 8120.(b) Liu, X. F.; Li, H. M.; Deng, L. Org. Lett. 2005, 7, 167.(c) Liu, Y. J.; Melgar-Fernandez, R.; Juaristi, E. J. Org. Chem.2007, 72, 1522.(d) Hasegawa, Y.; Watanabe, M.; Gridnev, I. D.; Ikariya, T. J. Am.Chem. Soc. 2008, 130, 2158.

[9] (a) Marigo, M.; Schulte, T.; Franzen, J.; J?rgensen, K. A. J. Am.Chem. Soc. 2005, 127, 15710.(b) Bertelsen, S.; Marigo, M.; Brandes, S.; Diner, P.; J?rgensen, K.A. J. Am. Chem. Soc. 2006, 128, 12973.(c) Galzerano, P.; Pesciaioli, F.; Mazzanti, A.; Bartoli, G.;Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 7892.

[10] (a) Jenner, G.; Papadopoulos, M. J. Org. Chem. 1986, 51, 585.(b) Poulsen, T. B.; Alemparte, C.; J?rgensen, K. A. J. Am. Chem.Soc. 2005, 127, 11614.(c) Leblanc, Y.; Zamboni, R.; Bernstein, M. A. J. Org. Chem. 1991,56, 1971.(d) Brimble, M. A.; Heathcock, C. H. J. Org. Chem. 1993, 58,5261.(e) Waser, J.; Carreira, E. M. J. Am. Chem. Soc. 2004, 125, 5676.(f) Waser, J.; Gonzalez-Gomez, J. C.; Nambu, H.; Huber, P.; Carreira,E. M. Org. Lett. 2005, 7, 4249.(g) Matsubara, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2006, 45,7933.(h) Chang, L.; Kuang, Y. L.; Qin, B.; Zhou, X.; Liu, X. H.; Lin, L.L.; Feng, X. M. Org. Lett. 2010, 12, 2214.

[11] (a) Cheng, L.; Liu, L.; Wang, D.; Chen, Y. J. Org. Lett. 2009, 11,3874.(b) Qian, Z. Q.; Zhou, F.; Du, T. P.; Wang, B. L.; Ding, M.; Zhao,X. L.; Zhou, J. Chem. Commun. 2009, 6753.(c) Bui, T.; Borregan, M.; Barbas, C. F. J. Org. Chem. 2009, 74,8935.(d) Bui, T.; Hernandez-Torres, G.; Milite, C.; Barbas, C. F. Org.Lett. 2011, 12, 5696.(e) Yang, Z. G.; Wang, Z.; Bai, S.; Shen, K.; Chen, D. H.; Liu, X.H.; Lin, L. L.; Feng, X. M. Chem. Eur. J. 2010, 16, 6632.(f) Mouri, S.; Chen, Z. H.; Mitsunuma, H.; Furutachi, M.;Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 1255.(g) Selvakumar, K.; Vaithiyanathan, V.; Shanmugam, P. Chem.Commun. 2010, 2826.

[12] (a) Lee, C. K.; Kim, S. J.; Hahn, C. S. J. Org. Chem. 1980, 45,1692.(b) Lee, C. K.; Ahn, Y. M. J. Org. Chem. 1990, 55, 3957.(c) Zaltsgendler, I.; Leblanc, Y.; Bernstein, M. A. Tetrahedron Lett.1993, 34, 2441.(d) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682.(e) Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268.(f) Brandes, S.; Bella, M.; Kj?rsgaard, A; J?rgensen, K. A. Angew.Chem. Int. Ed. 2006, 45, 1147.(g) Yu, W. Y.; Sit, W. N.; Lai, K. M.; Zhou, Z. Y.; Chan, A. S. C. J.Am. Chem. Soc. 2008, 130, 3304.

[13] (a) Brunn, B. E.; Huisgen, R. Angew. Chem. Int. Ed. 1969, 8, 513.(b) Kolasa, T.; Miller, M. J. J. Org. Chem. 1987, 52, 4978.(c) Liu, Y. X.; Xu, C. F.; Liu, L. Z. Synthesis 2003, 1335.(d) Otte, R. D.; Sakata, T.; Guzei, I. A.; Lee, D. Org. Lett. 2005, 7,495.(e) Nair, V.; Biju, A. T.; Abhilash, K. G.; Menon, R. S.; Suresh, E.Org. Lett. 2005, 7, 2121.(f) Nair, V.; Biju, A. T.; Vinod, A. U.; Suresh, E. Org. Lett. 2005, 7,5139.(g) Girard, M.; Murphy, P.; Tsou, N. N. Tetrahedron Lett. 2005, 46,2449.(h) Nair, V.; Mathew, S. C.; Biju, A. T.; Suresh, E. Tetrahedron Lett.2007, 48, 9018.(i) Nair, V.; Biju, A. T.; Mohanan, K.; Suresh, E. Org. Lett. 2006, 8,2213.(j) Nair, V.; Mathew, S. C.; Biju, A. T.; Suresh, E. Angew. Chem.Int. Ed. 2007, 46, 2070.(k) Moebs-Sanchez, S.; Bouhadir, G.; Saffon, N.; Maron, L.;Bourissou, D. Chem. Commun. 2008, 3435.(l) Morriso, D. C. J. Org. Chem. 1958, 23, 1072.

[14] (a) Cohen, B. S. G.; Zand, R.; Steel, C. J. Am. Chem. Soc. 1961, 83,2895.(b) Gillis, B. T.; Beck, P. E. J. Org. Chem. 1962, 27, 1947.(c) Allred, E. L; Anderson, C. J. Org. Chem. 1967, 32, 1874.(d) Marullo, N. P.; Alford, J. A. J. Org. Chem. 1968, 33, 2368.(e) Lahousse, H.; Martens, H. J.; Toppet, S.; Hoornaert, G. J. J. Org.Chem. 1982, 47, 2001.(f) Pindur, U.; Kim, M. H.; Rogge, M.; Massa, W.; Molinier, M. J.Org. Chem. 1992, 57, 910.(g) Avalos, M.; Babiano, R.; Cintas, P.; Clemente, F. R.; Jimenez, J.L.; Palacios, J. C.; Sanchez, J. B. J. Org. Chem. 1999, 64, 6297.(h) Minami, T.; Chikugo, T.; Hanamoto, T. J. Org. Chem. 1986, 51,2210.(i) Monbaliu, J. C.; Tinant, B.; Peeters, D.; Marchand-Brynaert, J.Tetrahedron Lett. 2010, 51, 1052.(j) Fitzsimmons, B. J.; Leblanc, Y.; Rokach, J. J. Am. Chem. Soc.1987, 109, 285.(k) Fitzsimmons, B. J.; Leblanc, Y.; Chan, N.; Rokach, J. J. Am.Chem. Soc. 1988, 110, 5229.(l) Leblanc, Y.; Fitzsimmons, B. J.; Springer, J. P.; Rokach, J. J. Am.Chem. Soc. 1989, 111, 2995.

[15] (a) Ma, S. M.; Jiao. N.; Zheng, Z. L.; Ma, Z. C.; Lu, Z.; Ye, L. W.;Deng, Y. Q.; Chen, G. F. Org. Lett. 2004, 6, 2193.(b) Yang, Q.; Jiang, X. F.; Ma, S. M. Chem. Eur. J. 2007, 13, 9310.(c) Cheng, X.; Ma, S. M. Angew. Chem. Int. Ed. 2008, 47, 4581.(d) Shu, W.; Yang, Q.; Jia, G. C.; Ma, S. M. Tetrahedron Lett. 2008,64, 11159.(e) Cheng, X.; Ma, S. M. Chem. Commun. 2009, 4263.(f) Cui, S. L.; Wang, J.; Wang, Y. G. Org. Lett. 2008, 10, 13.(g) Basavaiah, D.; Roy, S. Org. Lett. 2008, 10, 1819.

[16] (a) Wang, M. Z.; Xu, H. W.; Liu, Y. G.; Wong, M. K.; Che, C. M.Adv. Synth. Catal. 2006, 348, 2391.(b) Saleem, R. S. Z.; Tepe, J. J. J. Org. Chem. 2010, 75, 4330.(c) Su, Y. H.; Jiang, Z.; Hong, D.; Lu, P.; Wang, Y. G.; Lin, X. F.Tetrahedron Lett. 2010, 66, 2427.(d) Monge, D.; Jensen, K. L.; Marin, I.; J?rgensen, K. A. Org. Lett.2011, 13, 328.(e) Hong, D.; Zhu, Y. X.; Lin, X. F.; Wang, Y. G. Tetrahedron 2011,67, 650.

[17] (a) Achiwa, K.; Yamada, S. Tetrahedron Lett. 1974, 15, 1799.(b) Berlin, J. M.; Fu, G. C. Angew. Chem. Int. Ed. 2008, 47, 7048.(c) Huang, X. L.; Chen, X. Y.; Ye, S. J. Org. Chem. 2009, 74, 7585.(d) Wei, D. H.; Zhu, Y. Y.; Zhang, C.; Sun, D. Z.; Zhang, W. J.;Tang, M. S. J. Mol. Catal. A: Chem. 2011, 334, 108.(e) Allen, A. D.; Huang, W. W.; Moore, P. A.; Far, A. R.; Tidwell, T.T. J. Org. Chem. 2000, 65, 5676.

[18] (a) Yoneda, F.; Suzuki, K.; Nitta, Y. J. Am. Chem. Soc. 1966, 88,2328.(b) Yoneda, F.; Suzuki, K.; Nitta, Y. J. Org. Chem. 1967, 32, 727.(c) Hayashi, M.; Matsuura, Y.; Watanabe, Y. Tetrahedron Lett.2004, 45, 1409.(d) Cao, H. T.; Gree, R. Tetrahedron Lett. 2009, 50, 1493.

[19] (a) Xu, X. L.; Li, X. N.; Ma, L.; Ye, N.; Weng, B. J. J. Am. Chem.Soc. 2008, 130, 14048.(b) Xu, X. L.; Li, X. N. Org. Lett. 2009, 11, 1027.

[20] (a) Iranpoor, N.; Firouzabadi, H.; Khalili, D.; Shahin, R. TetrahedronLett. 2010, 51, 3508.(b) Reddy, B. V. S.; Reddy, S. M. S.; Madan, C. Tetrahedron Lett.2011, 52, 1432.

[21] (a) Guijarro, A.; Rieke, R. D. Angew. Chem. Int. Ed. 1998, 37,1679.(b) Velarde-Ortiz, R.; Guijarro, A.; Rieke, R. D. Tetrahedron Lett.1998, 39, 9157.(c) Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. J. Org.Chem. 1999, 64, 9189.(d) Takahashi, T.; Li, Y. Z.; Ito, T.; Xu, F.; Nakajima, K.; Liu, Y. H.J. Am. Chem. Soc. 2002, 124, 1144.(e) Mukaiyama, T.; Takahashi, K. Tetrahedron Lett. 1968, 9, 5907.(f) Hummel, G.; Hindsgaul, O. Angew. Chem., Int. Ed. 1999, 38,1782.(g) Uemura, T.; Chatani, N. J. Org. Chem. 2005, 70, 8631.(h) Kisseljova, K.; Tsubrik, O.; Sillard, R.; Maeorg, S.; Maeorg, U.Org. Lett. 2006, 8, 43.(i) Muniz, K.; Nieger, M. Angew. Chem. Int. Ed. 2006, 45, 2305.(j) Muniz, K.; Iglesias, A. Angew. Chem. Int. Ed. 2007, 46, 6350.

[22] (a) Axen, R.; Chaykovsky, M.; Witkop, B. J. Org. Chem. 1967, 32,4117.(b) Clarke, R. L.; Gambino, A. J.; Heckeler, M. L. J. Org. Chem.1978, 43, 4589.(c) Wamhoff, H.; Schupp, W. J. Org. Chem. 1986, 51, 2787.(d) Ohno, M.; Ishizaki, K.; Eguchi, S. J. Org. Chem. 1988, 53,1285.(e) Rieber, N.; Alberts, J.; Lipsky, J. A.; Lemal, D. M. J. Am. Chem.Soc. 1969, 91, 5668.(f) Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.;Sharpless, K. B. Angew. Chem. Int. Ed. 2005, 44, 3275.(g) Chen, Q. A.; Zeng, W.; Zhou, Y. G. Tetrahedron Lett. 2009, 50,6866.

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